Methanesulfonic Acid → 1-(Cyclopropylmethyl)-5-methoxy-1H-benzotriazole

HRID 872284Notes

Reaction equation

HRID 872284 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[C:7]([NH2:14])=[CH:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=2)[CH2:3][CH2:2]1.CS(O)(=O)=O.[N:20](OCCC(C)C)=O>C(O)C.C(OCC)(=O)C>[CH:1]1([CH2:4][N:5]2[C:6]3[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:7]=3[N:14]=[N:20]2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8053Isoamyl NitriteHCID 70197765HCID 70197765, compound

Product 1

HCID 686570341-(Cyclopropylmethyl)-5-methoxy-1H-benzotriazole

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N1-(Cyclopropylmethyl)-4-methoxybenzene-1,2-diamine (8-2, 10.8 g, 56.2 mmol) was dissolved in ethanol (80 mL) and treated with methanesulfonic acid (3.65 ml, 56.2 mmol) followed by isoamyl nitrite (7.56 ml, 56.2 mmol). The mixture was stirred for 15 minutes, diluted with ethyl acetate (1500 mL) and washed with saturated bicarbonate solution (500 mL×2). The organic extracts were concentrated in vacuo. The residue was purified by silica gel gradient chromatography (5-50% ethyl acetate in heptanes), providing the titled compound 8-3 as a tan solid.

Workup

  1. washwashed with saturated bicarbonate solution (500 mL×2)
  2. concentrationThe organic extracts were concentrated in vacuo
  3. customThe residue was purified by silica gel gradient chromatography (5-50% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-818a979a68cf411f9d9be0dae51dc961
Source dataset
uspto-grants-2015_03
Patent number
US08975286B2

Reaction notes

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